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Total synthesis of (.+-.)- and (-)-ptilocaulin
Journal article   Peer reviewed

Total synthesis of (.+-.)- and (-)-ptilocaulin

Barry B Snider and William C Faith
Journal of the American Chemical Society, Vol.106(5), pp.1443-1445
03/01/1984
DOI: https://doi.org/10.1021/ja00317a042

Abstract

Ptilocaulin Chemical Synthesis Stereochemistry
An efficient five-step synthesis of (±)-ptilocaulin (1) is described. The key step is the addition of guanidine to enone 2 to give 1. An analogous five-step synthesis of (-)-ptilocaulin (16) from (/?)-5-methyl-2-cyclohexenone (11) establishes the absolute stereochemistry of natural (+)-ptilocaulin as 1.

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